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| Formula | C23H38O2 |
| Molar mass | 346.555 g·mol−1 |
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(C9)-CP 47,497 (CP 47,497 dimethylnonyl homologue) is a synthetic cannabinoid, a CP 47,497 homologue. [1]
Its systematic name is 2-[(1S,3R)-3-hydroxycyclohexyl]-5-(1,1-dimethylnonyl)phenol.
Cannabinoids are several structural classes of compounds found in the cannabis plant primarily and most animal organisms or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (delta-9-THC), the primary psychoactive compound in cannabis. Cannabidiol (CBD) is also a major constituent of temperate cannabis plants and a minor constituent in tropical varieties. At least 113 distinct phytocannabinoids have been isolated from cannabis, although only four have been demonstrated to have a biogenetic origin. It was reported in 2020 that phytocannabinoids can be found in other plants such as rhododendron, licorice and liverwort, and earlier in Echinacea.
CP 55,940 is a synthetic cannabinoid which mimics the effects of naturally occurring THC. CP 55,940 was created by Pfizer in 1974 but was never marketed. It is currently used as a research tool to study the endocannabinoid system.
Tetrahydrocannabivarin is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of pentyl (5-carbon), making it non-psychoactive in lower doses. It has been shown to exhibit neuroprotective activity, appetite suppression, glycemic control and reduced side effects compared to THC, making it a potential treatment for management of obesity and diabetes. THCV was studied by Roger Adams as early as 1942.
HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-myrtenol by a group led by Raphael Mechoulam at the Hebrew University. HU-210 is 100 to 800 times more potent than natural THC from cannabis and has an extended duration of action. HU-210 has a binding affinity of 0.061 nM at CB1 and 0.52 nM at CB2 in cloned human cannabinoid receptors compared to delta-9-THC of 40.7 nM at CB1. HU-210 is the (–)-1,1-dimethylheptyl analog of 11-hydroxy- Δ8- tetrahydrocannabinol; in some references it is called 1,1-dimethylheptyl- 11-hydroxytetrahydrocannabinol. The abbreviation "HU" stands for Hebrew University.
Levonantradol (CP 50,556-1) is a synthetic cannabinoid analog of dronabinol (Marinol) developed by Pfizer in the 1980s. It is around 30 times more potent than THC, and exhibits antiemetic and analgesic effects via activation of CB1 and CB2 cannabinoid receptors. Levonantradol is not currently used in medicine as dronabinol or nabilone are felt to be more useful for most conditions, however it is widely used in research into the potential therapeutic applications of cannabinoids.
Δ9-Tetrahydrocannabutol is a phytocannabinoid found in cannabis that is a homologue of tetrahydrocannabinol (THC), the main active component of Cannabis. Structurally, they are only different by the pentyl side chain being replaced by a butyl side chain. THCB was studied by Roger Adams as early as 1942
JWH-073, a synthetic cannabinoid, is an analgesic chemical from the naphthoylindole family that acts as a full agonist at both the CB1 and CB2 cannabinoid receptors. It is somewhat selective for the CB1 subtype, with affinity at this subtype approximately 5× the affinity at CB2. The abbreviation JWH stands for John W. Huffman, one of the inventors of the compound.
CP 55,244 is a chemical compound which is a cannabinoid receptor agonist. It has analgesic effects and is used in scientific research. It is an extremely potent CB1 full agonist with a Ki of 0.21 nM, making it more potent than the commonly used full agonist HU-210.
CP 47,497 or (C7)-CP 47,497 is a cannabinoid receptor agonist drug, developed by Pfizer in the 1980s. It has analgesic effects and is used in scientific research. It is a potent CB1 agonist with a Kd of 2.1 nM.
Synthetic cannabinoids are a class of designer drug molecules that bind to the same receptors to which cannabinoids in cannabis plants attach. These novel psychoactive substances should not be confused with synthetic phytocannabinoids or synthetic endocannabinoids from which they are in many aspects distinct.
Cannabicyclohexanol is a cannabinoid receptor agonist drug, developed by Pfizer in 1979. On 19 January 2009, the University of Freiburg in Germany announced that an analog of CP 47,497 was the main active ingredient in the herbal incense product Spice, specifically the 1,1-dimethyloctyl homologue of CP 47,497, which is now known as cannabicyclohexanol. The 1,1-dimethyloctyl homologue of CP 47,497 is in fact several times more potent than the parent compound, which is somewhat unexpected as the 1,1-dimethylheptyl is the most potent substituent in classical cannabinoid compounds such as HU-210.
Canbisol (Nabidrox), is a synthetic cannabinoid derivative that is the dimethylheptyl homologue of 9-nor-9β-hydroxyhexahydrocannabinol (HHC). It is a potent agonist at both the CB1 and CB2 receptors, with a binding affinity of 0.1 nM at CB1 and 0.2 nM at CB2. It is mainly used in scientific research, in receptor binding studies to determine the structure and function of the cannabinoid receptors, but has been made illegal in some countries due to its possible abuse potential as a cannabinomimetic drug.
HU-243 (AM-4056) is a synthetic cannabinoid drug that is a single enantiomer of the hydrogenated derivative of the commonly used reference agonist HU-210. It is a methylene homologue of canbisol. It is a potent agonist at both the CB1 and CB2 receptors, with a binding affinity of 0.041 nM at the CB1 receptor, making it marginally more potent than HU-210, which had an affinity of 0.061 nM in the same assay.
RCS-4, or 1-pentyl-3-(4-methoxybenzoyl)indole, is a synthetic cannabinoid drug sold under the names SR-19, BTM-4, or Eric-4, but originally, OBT-199.
(C6)-CP 47,497 is a synthetic cannabinoid, a CP 47,497 homologue.
O-1871 is a potent cannabinoid agonist which was invented by Billy R Martin and Raj K Razdan at Organix Inc in 2002. It has a CB1 receptor affinity of 2.0 nM and a CB2 receptor affinity of 0.3 nM. Structurally, O-1871 is a cyclohexylphenol derivative related to CP 47,497, and so is illegal in some jurisdictions where CP 47,497 and its derivatives are banned. However the 3,3-dimethylcyclohexyl substituent of O-1871 can be replaced by various other groups, producing other potent compounds such as the cycloheptyl derivative O-1656 and the 2-adamantyl derivative O-1660, as well as the corresponding 3,5-dichlorophenyl derivative, which are not cyclohexylphenol derivatives.
Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB1 and CB2 agonist which was known as a synthetic homologue of THC, but for the first time in 2019 was isolated as a natural product in trace amounts from Cannabis sativa. It is structurally similar to Δ9-THC, the main active component of cannabis, but with the pentyl side chain extended to heptyl. Since it has a longer side chain, its cannabinoid effects are "far higher than Δ9-THC itself." Tetrahydrocannabiphorol has a reported binding affinity of 1.2 nM at CB1, approximately 33 times that of Δ9-THC (40 nM at CB1). THCP was studied by Roger Adams as early as 1942.
Tetrahydrocannabihexol is a phytocannabinoid, the hexyl homologue of tetrahydrocannabinol (THC) which was first isolated from Cannabis plant material in 2020 along with the corresponding hexyl homologue of cannabidiol, though it had been known for several decades prior to this as an isomer of the synthetic cannabinoid parahexyl. Another isomer Δ8-THCH is also known as a synthetic cannabinoid under the code number JWH-124, though it is unclear whether this occurs naturally in Cannabis, but likely is due to Delta-8-THC itself being a degraded form of Delta-9-THC. THC-Hexyl can be synthesized from 4-Hexylresorcinol and was studied by Roger Adams as early as 1942.
ADB-HEXINACA is a cannabinoid designer drug that has been found as an ingredient in some synthetic cannabis products, first appearing in early 2021. It is a longer chain homologue of previously encountered synthetic cannabinoid compounds such as ADB-BUTINACA and ADB-PINACA.
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